Parasiticidal preparations



Patented Feb. 6, 1945 UNITED STATE s PATEN 3 .667 mnasrrrcmsr. rnnrm'rrous Elbert G- Ladd, Passaic, N; 1., assiznor to United States Rubber Company, New York, N. Y., a

T .oF-Fic corporation oi New Jersey No- Drawing. ApplicationMay s, 1943,

Serial No. 485,888

\ 5 Claims. (on 161-32)- This invention relates to new and US$17.11" improvements in parasiticid'al preparations, more particularly to fungicides, and insecticides, the

' latter term being considered to include larvicides and arachnicides, as well as insectifuges and larvifuges. The invention further relates to other materials.

I have found that 2,2,3,3-tetrachloro-1,2,3,i-

tetrahydronaphthalene-dione-1,4 is an effective.

-methcds of protecting organic material subjectto attack by microorganisms, as in the-immunizing of seed, and the mildewproofing of fabrics and infested with a number of organisms, including Putin-um ultimum. The effectiveness of the fungicide was determined by comparing the number of treated seeds which germinated and developedinto healthy plants with an equal number of untreated seeds planted under the same condi-- tions. Observation made at the end of ten days v showed that.98'% of the treated seeds had gerflminated. and grown into disease-free seedlings,

whereas only 49% of the untreated, seed had germinated. The untreated seeds'which did not ger minate, and the seedings which developed from fungicide and insecticide. The structure of the 7 compound may be represented as follows:

I Cl

tetrahy dronaphthalin.

The 2,2,3,3-tetrachloro-1,2,3,4-tetrahydronaphthalene-dione -l,4 may be used as a seed protectant and to protect plants or soil from organisms harmful to seeds and plants. Itmay als be ap plied to prevent or retard fungus growth and the formation of, for example, mildew on rope, wood, fur, hair, feathers, cotton, wool, leather, rubber, rubberized or synthetic resin-coated fabrics,and the like. The 2,2,3,3-tetrachloro-1,2,3,4-tetrahydronaphthalene-dione-L4 may be applied as' dust or sprays or in solution in a suitable solvent. It may be applied diluted or undiluted, Or mixed with carrier, or other fungicides or insecticides, fertilizers, hormones, agents.

The following examples are given to illustrate the invention.

. Example! Pea seed, variety Perfection, were tumbledwith 1% by weight of the 2,2,3,3-tetrachloro-1,2,3,4-

buflering or safening the untreated seeds, were observed to be infected with Puthium ultimum which had caused seed and seedling rot, whereas-those which were treated with 2,2,3,3-tetrachloro-l,2,3,4-tetrahydronaphthalene-dione-L4 were free of this disease.

- Example II In this case a piece of cotton fabric was dipped 'into a 1% solution, oi- 2,2,3,3;-tetrachloro-l,2,3,4-

tetrahydronaphthalene-dione-1,4 in benzene and V then allowed to dry. The fabric sample was then then sprayed on bean plants heavily infested with tetrahydronaphthalene-dime-1,4 vin dust .form.

' divided into sections.

, One section was inocculated with Chaetomium alobomm spore suspension and incubated on agar medium immediately after treatment and drying; the other was inocculated and incubated in a similar manner after soaking sixteen hours in water and being dried. The sections were incubated for thirty- Iour days. No growth appeared in either, section.

In control cotton fabrics which were not treated.

Example III The arachnicidal properties of 2,2,3,3-tetra chloro-l, 2, 3, 4-tetrahydronaphthalenedione-1,4 are shown by the following test:

-1 :part by weight of 2, 2, 3, '3-tetrachloro- 1,2,a,4-'

tetrahydronaphthalenedione-1,4 was suspended in 200 parts of water whichcontained part of Nacconal (wetting agent). The dispersion was red spiders. Countstaken 72 hours after spraying showed that 99% of the spiders had been killed.

,A similar experiment in which the dilutionwas increased to 1 part of the chemical in 400 parts of water containing .001 part Nacconal gave 96% mortality. Counts taken on control plants intested with spiders which were sprayed with water containing .25% of Nacconal but without 2 v the 2, 2, 3;3-tetrachloro-1,2,3,4-tetrahydrcnaphthalenedione-1,4 showed less than 10% dead.

Example IV The repellent properties of 2,2,3,3-tetrach1oro- 1,2,3,4 tetrahydronaphthalene-dione 1,4 are shown by the following tests:

4 pieces of woolen cloth 1 x4" were immersed in a 5%:solution by'weight of the chemical in ether until" saturated with the solution, then removed, air-dried to remove the ether and each placed in a separate covered petri dish contain; ing 5 black carpet beetle larvae and allowed to 1 stand in a dark place at room temperature for Four similar pieces of untreated three weeks.

woolen cloth were placed in separate petri dishes,

each of which contained five black carpet beetle larvae and then allowed to stand for the same length of time under the same conditions. At the end of this period it was found that no visible.

feeding had occurred on the treated samples whereas very' heavy feeding had occurred on the untreated samples. Furthermore, 70% 0f the larvae exposed tot'h'e treated samples were dead, whereas there was no mortality in the larvae exposed to the-untreated samples.

subject to attack by microorganisms which comprises treating said organic material with 2,2,33,3- tetrachloro 1,2,3,4 tetrahydronaphthalenedione-1,4.

" *3. The-method of protecting seeds, [plants and soil subject to attack by fungi and insects which comprises treating said material with 2,2,33-

tetrachloro 1 ,2,3,4 tetrahydronaphthalenedime-1,4, Y 4. The method of immunizing seed which comprises treating said seed with 2,2,3,3-tetrachloro- 1,2,3, 4-,tetrahydronaphthalene-dione-L4.

5. The method of controlling mildew on organic material-which comprises treating said organic material with 2,2,3,3-tetrachloro-I,2,3,4-tetrahydronaphthalene-dione-1,4.

- ELBERT C. LADD. 

